反应详情

4-(mercaptomethyl)benzoic acid (36, 500 mg, 2.97 mmol) was dissolved in water (10 mL) and cooled in an ice bath. The cooled solution stirred as methyl methanethiolsulfonate (413 mg, 3.27 mmol) dissolved in ethanol (5.00 mL) was added. Following addition, the cooling bath was removed and the reaction was stirred overnight at room temperature. After proceeding overnight, the reaction was diluted with saturated sodium chloride and extracted with ether. The combined extracts were washed with sodium chloride, dried over anhydrous sodium sulfate and concentrated in vacuo. The product was isolated using silica flash chromatography eluting with a gradient of 40-60% ethyl acetate in hexanes containing 1% acetic acid over 20 min. to give 482 mg of the desired product, 4-((methyldisulfanyl)methyl)benzoic acid (37b), in 73.5% yield. 1H NMR (CDCl3) δ 2.121 (3H, s), 3.938 (2H, s), 7.457 (2H, d, J=8.4 Hz), 8.068 (2H, d, J=8 Hz).

1. temperaturecooled in an ice bath
2. additionwas added
3. additionaddition
4. customthe cooling bath was removed
5. waitAfter proceeding overnight
6. additionthe reaction was diluted with saturated sodium chloride
7. extractionextracted with ether
8. washThe combined extracts were washed with sodium chloride
9. dry with materialdried over anhydrous sodium sulfate
10. concentrationconcentrated in vacuo
11. customThe product was isolated
12. washeluting with a gradient of 40-60% ethyl acetate in hexanes containing 1% acetic acid over 20 min.